When we are starting out we want to say yes to everything because we want or need the revenue. I said yes to work that wasn’t aligned with my overall business plan. This is a real problem and I don’t have a solution for it but I will say that once you have enough in the pipeline to start saying no, you should start saying no!
As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Dorothy Kolb. After a foundational start at Deloitte and building a 20+ year career in media finance & operations across notable companies including CBS Sports, FOX Sports, NBC & HGTV/Food Network, Dorothy launched dk east associates to bring her world-class background to emerging businesses to help them grow to their fullest potential through outsourced CFO, accounting strategy and HR services. Dorothy understands the importance of balancing things in life: She became an entrepreneur while raising her 4 teenage sons (including twins!) as a single mom. Part strategist, part basketball coach, part founder!
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I never intended to become an entrepreneur. I’m not like many others in this who came from long lines of entrepreneurial thinkers. I was in corporate entertainment for 20+ years and then was working for a sports league company when I was downsized out of my CFO position. The beauty of that last job was that the whole company was 100% virtual. I was a newly single (divorced) mother of 4 sons and didn’t know how I could work in a company that required a long commute and long hours. So I took what was previously a small side hustle of doing accounting work and turned it into my full time gig. I started actually with a few bookkeeping clients but those clients quickly figured out that I had a lot more to offer. They in turn referred their colleagues to me and what was a panic-stricken necessity became an actual viable business.
Can you share the most interesting story that happened to you since you began leading your company?
I was a completely accidental entrepreneur. I was downsized from my job and was a newly divorced mother of 4 with no financial support. I went into this from a place of necessity. What was most interesting was that once I established myself, I found founders coming to me saying they “had to work with me.” It was so amazing to go from not knowing what I was doing to a place of being sought out because I did what I do so well.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Oh! One of my first pitches was to a start-up in the medical field. Unfortunately, I completely misunderstood what the overall product and business plan was and when I sent over my proposal, the founder thanked me for a future business idea but it wasn’t what they were doing now. I don’t know how I was so off-base but I learned to really listen and ask questions during initial consult calls — not only to propose the right services but also to make sure I’m working within my wheelhouse. I also learned it’s okay to say no and recommend a colleague who is a better fit.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
My significant other is a huge supporter of mine. He had unwavering faith that I would be able to do this even when I struggled and thought I should go back to a regular full-time job. We are bi-coastal so it wasn’t that he was physically with me, but there were (and still are) daily morning text messages of positive encouragement. He also was my original financier by giving me just a small seed fund. It really buoyed me emotionally knowing someone had confidence in my plan.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?
I think that, up until this pandemic, it was frowned upon to merge your family life with your professional life. I remember back in my corporate days barely acknowledging that I had children because that might appear weak or that I had other priorities. I think many women still feel that they won’t be taken seriously if they have to balance family life with their business goals. I also think many women are actually not taken seriously by the bigger VC and investor shops because they are focused on white male founders — mostly because that is familiar to them. We need more women to lead or start funds that target women-owned businesses and we need more education and training for women to be confident in having their conversations with a boardroom full of men until those tides have turned.
Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?
I would love to see more classes in college aimed specifically at women on how to find funding and how to really walk through that process with the lens of being a woman. I think having programs that identify and connect both sides of the table would be a fantastic way to facilitate this process. Incentivizing the VC’s in some way to target more women-owned businesses so that they are actively seeking out these types of opportunities rather than leaving it to the women-owners to initiate the discussions would be a real step forward as well.
This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?
Women approach business from a different perspective from men. We tend to look at things in a more holistic way, combining not only financial gains but emotional and societal gains. Women are often far more collaborative which leads to synergies that might not be otherwise pursued. To that end, women should become founders so that we, on a very basic level, create a better world for future generations. On a more granular level, women founders are open to a much more flexible lifestyle which allows them to more easily combine being a parent and a business owner. It allows us to step away from the corporate views of employees which tends to lean heavily towards the “you’re expendable” which adds exponentially to our imposter syndrome. Leading your own company allows you to create your own culture and your own shared values so that your daily work aligns with your inner priorities.
What are the “myths” that you would like to dispel about being a founder. Can you explain what you mean?
Oh, the myth that things will just get done without a plan is one of them.
I found personally that the idea that customers/clients will just come along without any active marketing or networking was so far off. You cannot just assume people will hear about you — at least not in the initial years. I really wish I had engaged with my fractional chief marketing officer so much sooner. Getting my messaging and branding aligned with what I really wanted to do and what I really wanted to attract was paramount to my business success. Another is the thought that you will bring along process and structure “when we get bigger and need it” is a huge myth. To get these things in place before you need them is key. Scaling is infinitely easier when you have structure in place that is organized, functional and grows with you. Retroactively building these things when you’re already big and feeling the strain is costly. Think of the old adage — pay me 1 dollar now or 1,000 dollars later. Fixing issues when they are already integrated into your whole business is time consuming, hinders business growth and costs a lot more than building it out and having it grow along with you.
Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?
I don’t think everyone is cut out for it. I don’t like to say that but I’ve seen too many founders who were amazing people with great ideas but just couldn’t wrap their heads around making it profitable. Often, that can mean they can’t retain their top talent because those employees are too concerned about their paychecks not clearing. Some founders forget to feed their company while they’re feeding everyone else with their services. Being a founder is a stressful role. You need to be able to roll with the punches, make decisions quickly and facilitate a company culture that is conducive to success. Success is not only monetary but in creating something that is beneficial to the greater good.
Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why?
- I wish someone told me that marketing was more than advertising.
I had mistakenly merged marketing and advertising in my own head. I thought it was all about buying ads on social media or sending out direct mail. After I hired my CMO, I realized how far off I was in my messaging from what I was actually trying to attract. I realized that I had to be consistent across all platforms and media because frequency of the same message was key. Once I started getting that in order, I began to attract the clients I wanted which led to more referrals and more of the types of clients that I wanted. Marketing is like tapping into the law of attraction. You put out what you want and it comes to you.
2. I wish someone told me to outsource sooner.
It’s so hard to let go, right? We think we can and should be doing all of the things better than anyone else can because they don’t understand what we are trying to accomplish. But that is not correct. We need to put ourselves in our highest and best use. I began with outsourcing my marketing, then my social media management and then my administrative work (with a VA). I was immediately freed up to do the work I actually love to do and my outsourced team did the same. We all were elevated.
3. I wish someone told me to trust myself more.
Imposter syndrome is real. It doesn’t matter how or when you started dragging that baggage around with you. It could be from childhood or your history of corporate employers who made you feel like you were lucky to have a job. I felt the same. Initially, I was always checking with others to see if I had made the right decision, but the right decision is personal and others can’t make that choice for you. Once I trusted myself and my experience, I became a better consultant for my clients because I had confidence in myself which became an intangible personal asset.
4. I wish someone told me I should say “no” more often.
Oh this one! When we are starting out we want to say yes to everything because we want or need the revenue. I said yes to work that wasn’t aligned with my overall business plan. This is a real problem and I don’t have a solution for it but I will say that once you have enough in the pipeline to start saying no, you should start saying no! As with the outsourcing I mentioned above, saying “no” allowed me to do my highest and best with work that makes me happy. My late father said he would have paid his employer to work there because he loved his job so much. Saying “no” gives me that same outlook — I look forward to going to work each day and I love my job.
5. I wish someone told me to invest in myself as well as my business.
It feels so selfish to invest in ourselves. We invest in software, process, inventory, location, other people but we forget to invest in the biggest asset we have — ourselves. I’ve allowed myself to take courses and certifications that added to my confidence and helped dissolve that aforementioned imposter syndrome. It also led to some really interesting connections with others that were in the same programs.
How have you used your success to make the world a better place?
I’ve helped other women founders be successful. I’m typically brought in at a time when they aren’t sure if their business should continue on and they have no one guiding them (great bookkeeper, great tax person but no strategist). I absolutely love it when I can help them see that they have a great thing and just a few tweaks to the business model turns it into something sustainable and profitable. Many of my clients are in the social impact space so when they do well, they are pushing forward an agenda that benefits all of us.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
I would love to see a movement to encourage high school entrepreneurship programs. There are vocational programs that include everything from auto mechanics to dance but what we really need is a program aimed at preparing students to be successful with their own businesses. Frankly, I think all students would benefit from this!
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.
I’ve been a fan of Marcus Lemonis for years. I love the way he approaches business and considers all the facets of a company (people, product, profits) as a holistic endeavor. I would love to be able to work on a project with him! I also really admire Sara Blakely. She’s an incredible leader. She’s authentic. She represents what women founders should strive to be.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.